


Casual Encounters

by suffocatingrelief



Category: Supernatural
Genre: Alive Mary Winchester, Alternate Universe - Human, Asexual Castiel (Supernatural), Craigslist, Criminal Castiel, Everyone is a little shit at some point, F/M, Good Parent John Winchester, Lawyer Lucifer (Supernatural), Lawyer Michael, Lawyer Sam Winchester, M/M, Mechanic Dean Winchester, Sensitive Dean Winchester, Sober Dean, Thanksgiving
Language: English
Status: In-Progress
Published: 2017-04-04
Updated: 2018-05-10
Packaged: 2018-10-14 20:39:18
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 6,029
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10544000
Author URL: https://archiveofourown.org/users/suffocatingrelief/pseuds/suffocatingrelief
Summary: Dean Winchester was not lonely. He wasn’t annoying or ugly. Dean was a pretty cool guy. Too bad no cute guys in a 100-mile radius had realized that, yet. In all honesty, Dean was pretty great. He had a nice job, a nice car, and he wasn’t bad on the eyes. So, why was he sitting on his couch eight days before Thanksgiving, scrolling through the “casual encounters” page on Craigslist? Shut up.(Tags will be added as written)





	1. Thankful for Craigslist

**Author's Note:**

> This was inspired by a screenshot of a Craigslist ad I saw on Tumblr.
> 
> Kudos and comments are my life force and will get stories updated sooner. (Just saying.)

**Notes for the Chapter:**

> If you recognize Dean's number, we're best friends. There is no choice.

 

 

     Dean Winchester was not lonely. He wasn’t annoying or ugly. Dean was a pretty cool guy. Too bad no cute guys in a 100-mile radius had realized that, yet. In all honesty, Dean was pretty great. He had a nice job, a nice car, and he wasn’t bad on the eyes. So, why was he sitting on his couch five days before Thanksgiving, scrolling through the “casual encounters” page on Craigslist? Shut up.

  
     “This is my life now, Honeybee.” Dean turned to his kitten (yeah, macho man, Dean Winchester, has a kitten named Honeybee. Crazier things have happened), who was curled up beside him, and hung his head in shame before resuming his pathetic scroll of shame. “All this and I still show up home with empty arms on Thanksgiving. I can hear Sam’s bad jokes already.”

     After what felt like forever of scrolling through admittedly uncomfortable descriptions of the “encounters” some people were looking for, Dean found one listing that piqued his interest. The listing was titled, “Alone on Thanksgiving? Mad at your dad? I can help.” Figuring it couldn’t hurt just to see what the original poster had to say, Dean clicked on the link and he was in a fit of laughter from the beginning. How could this guy be serious?

 

_I am a 28 year old felon with no high school degree, and a dirty old van one year younger than me painted like Eddie Van Halen’s guitar. I can play anywhere between the ages of 20 and 29 depending on if I shave. I’m a line cook and work late nights at a bar. If you’d like to have me as your strictly platonic date for Thanksgiving, but have me pretend to be in a very long or serious relationship with you, to torment your family, I’m game._

  
_I can do these things, at your request:_

  
_openly hit on other guests while you act like you don’t notice._

  
_start instigative discussion about politics and/or religion._  
_propose to you in front of everyone._

  
_pretend to be really drunk as the evening goes on (sorry, I don’t drink, but I used to. A lot. Too much in fact. I know the drill)._

  
_start an actual physical fight with a family member. either inside or on the front lawn for all the neighbors to see._

  
_I require no pay but the free meal I will receive as a guest!_

  
   
     Dean was in tears of laughter by the time he finished reading. He could just picture this guy trying to talk politics to his dad or hitting on one of his family members in front of his mother. And this guy was willing to do all of that for a free meal? Holy Jesus on a toothpick, this guy was nuts. After he finished laughing, Dean turned his phone off, picked up Honeybee, and saw himself off to bed. And if all he dreamt of were hilarious Thanksgiving dinner scenarios, no one had to know.

     When Dean got up the next morning and turned on his phone, his body and mind felt heavier. His phone had a few notifications, all of them text messages from his mom, saying how excited she was for him to come home for Thanksgiving. The dreaded family holiday was officially four days away and Dean had no one to show off to his family. At least Sam had Jess and Adam had Michael. Dean was 26 and was still perpetually alone.

     As he went through his morning routine, he humored the idea of actually bringing Craigslist Guy (he didn’t put his name in the listing so that’s what Dean named him) with him. If anything, Dean could just take him as a friend, which was much more than he had at the moment. Halfway through his bowl of cereal, Dean looked at Honeybee, who was curled up in front of the fireplace, and let outa sound that was somewhere between a sigh and a groan.

     “Fuck it.” Dean grabbed his phone off of the table and pulled back up the listing from the night before. After wrestling with his mind over how in the hell he was supposed to word his message, he finally typed something up and sent it out before throwing his phone at the couch to finish getting ready.

 

**Sent:** Hello. I’m messaging you about the Thanksgiving thing. Just wondering if someone’s already filled the spot or if you’re still free.

 

      Once Dean was finished getting ready and heading out the door, he picked his phone up to find that the guy had responded to his message.

 

**_Received:_** Hello. No, I’m still free, if you’re interested.

  
**Sent:** Sounds good. Just to avoid calling you Craigslist Guy, what’s your name?

  
   
      Dean’s phone dinged again as he was getting in his car.

 

_**Received:**_ Castiel. What’s your name? So I can stop calling you Thanksgiving Guy.

  
**Sent:** Dean. Hey, is it cool if I give you my number so we can talk about meeting up to go over details?

  
   
      Dean’s phone went off as he was driving but he waited until he got to work to check it.

 

**_Received:_** That seems agreeable.

  
**Sent:** Okay. It’s 678-999-8212. Talk to you later, Cas :)

 

     As he walked into the garage, he mentally scolded himself for using a smiley-face in a text message. For Christ’s sake, he was almost 30. His thoughts were cut short when a strong hand clapped him on the back.

     “Hey, brotha. You look mighty happy today.” That was Dean’s ‘kind of-friend’ Benny. They worked together and they hooked up once while they were both black-out drunk. It wasn’t that Dean didn’t want to be friends with the guy, it was that didn’t know how to be friends with people. He had a hard time finding people that shared his interests.

     “Morning, Benny. Just well rested, is all.” Dean hid his discomfort and changed into his coveralls before sliding underneath a jacked-up car and beginning his work day. By the time his lunch break rolled around, Dean sat in the break room and pulled out his phone to see that he had a text message from an unknown number.

 

_**Unknown:**_ Hello, Dean. I had no clue when ‘later’ was so I didn’t know how long I was supposed to wait. But, now you have my number so you can text me when you feel like it.

  
**Dean:** Hey, Cas. Yeah, sorry, ‘later’ is kind of a vague window I guess.

  
_**Cas:**_ Yeah it kinda is lol. Hey, would you mind to send me a picture of you so I know I’m not talking to a 50 year-old crazy man?

 

     Dean wrestled with himself once again and decided to just send a picture. He snuck out of the break room and into the bathroom, locking the door behind him. After finding a good angle that wasn’t too sweaty or oil smudge-y, he took a picture of himself and sent it, not giving himself a chance to chicken out.

 

**Dean:** [image attached]

 

 Dean’s lunch break ended 15 minutes later and Cas still hadn’t responded. Dean took that as a sign that Cas was not interested in being his platonic or not-platonic date. Oh well, there’s always Plan B (also known as, show up alone and get super drunk). A few minutes after he had gone back to work, Dean’s phone chirped, letting him know he got a text.

 

_**Cas:**_ Dean, I just spent 20 minutes trying to reverse image search that photo because there is no way you actually look like that.

 

 Dean’s cheeks heated up and flushed a bright red, much to his chagrin. Dean knew he wasn’t ugly but something about someone else complimenting him added a different feeling to it.

 

**Dean:** Now it’s your turn, dude.

  
_**Cas:**_ [image attached]

  
**Dean:** We should definitely meet up to discuss this.

  
_**Cas:**_ Ha okay. Roadhouse @ 8 tonight?

  
**Dean:** It’s a date.

**Notes for the Chapter:**

> Please tell me what you think!


	2. Thankful for The Roadhouse

**Summary for the Chapter:**

> Dean and Cas meet.

**Notes for the Chapter:**

> GUYS I FINALLY REWROTE THIS!!! It's still not a finished work but at least I'm happy with how it is written and where the story is going now. Please leave kudos and comments to let me know what you guys think!

     By the time 8 o'clock rolled around, Dean was walking in the front doors of the Roadhouse, a bar and grill his aunt and uncle own, and surveying the crowd to see if Cas had shown up already. He nervously adjusted the sleeve of his soft, worn flannel and chastised himself for wearing the exact same thing he started in after spending two hours fretting over what he should wear. That was crazy in and of itself. This wasn't a date. It was just a meeting...with a super hot guy...who will be spending a whole three days in close-quarters with him. Fuck. Okay, that made it worse. After a glance around, Cas was no where to be found so Dean wiped his sweaty palms off on his jeans and nervously walked up to the bar and a familiar blonde head turned around.  
 

     "Hey, Dean, long time no see." That's Joanna Beth Harvelle-Singer. The way she looked had everyone believe that a bar would be the last place you would find her. She looked like an honest-to-God cherub but don't ever say that to her face. Jo has a knife collection and a sawed-off shotgun (illegal, by the way) that she was more than willing to whip out on anyone. Yeah, she was that cousin and Dean wouldn't have her any other way. She was the perfect balance to his soft side and knew how to keep him sane and in-line.  
 

     "Hey, Joanna." Instant regret punched Dean right in the arm. That regret was named Jo. That girl has a mean right hook and man, when did she start wearing that many rings?  
 

     "Don't call me that, bitch." Jo had a mean bitch-face but she finally broke into a smile and she pulled a glass out from under the bar and a bottle of whiskey from the shelf. But before she could pour it, Dean put his hand over the glass.  
 

     "Ah, no thanks, Jo." That definitely raised an eyebrow or two. You see, Dean hadn't been to the Roadhouse in a while because four months ago, Dean got sober. Yes, sir, he did. And being around a bar certainly wasn't the smartest move for a recovering alcoholic. Dean hadn't always been a kitten-owning softie. But, that's a long story for later.  
 

     "That's new." Jo took the glass back and put the bottle away, instead opting to pour Dean a glass of water.  
 

     "Sure is. Now, I've gotta scram. I'll order something in a bit." Dean picked up his glass and nodded in Jo's direction before turning away from the bar, only to be stopped once again.  
 

     "Oh, hell no. I need details, Deanna." Jo slapped her hands onto the bar and stood in silence, daring Dean to try and walk away without saying anything.

  
     "Don't be like that, Jo. I'm just meeting a friend." Dean knew he was blushing but trying to cover it would be even more obvious so he decided to just hope she would accept that as an answer. Thankfully, today was his lucky day.

     "Hmm. I'll accept that. But if you let Ash take your table then we aren't cousins anymore."  
 

     "Wouldn't dream of it, Jo-Beth." Dean quickly walked away before Jo could hit him again and made his way to the booth farthest from the bar, still able to hear her threats from behind him. As he took a seat in the booth, his nerves only got worse. For a few moments, he considered hauling ass straight out of the bar and all the way back to his apartment. That plan was quickly cancelled when Dean caught sight of Cas enter from across the restaurant and fuck, he looked even better in person with his sex hair (yeah, yeah vulgar whatever), chapped-looking lips, and - wow, his eyes were even bluer in person (like the bluest blue to ever blue...shut up, that's a thing). He saw Cas wander a little aimlessly and made to get up to greet him until the other man caught his eye and made his way over. He got a much better view of Cas as he approached and he was even more satisfied. The waistcoat and tight-fitting (like, inappropriately tight) slacks were definitely a good choice, a much better one than what Dean decided to go with.  
 

     "Hello, Dean."  
 

     Nope. No. Vetoed. Absolutely not. That's cancelled. It's finished. It's over. It's all done. No more. It's not happening anymore. This is no longer occurring. Terminated. This has come to an end. Son of a bitch. This is not allowed. Cas isn't allowed to waltz in here looking like Professor Sex-on-a-Stick and have that voice to go along with it. It sounds like he's fucked out and just downed a glass of moonshine. This is not okay. Dean is not going to be able to tolerate this for three days straight without going through underwear like a teenager. He has to stop this before it starts.  
 

     "Hey, Cas." Dammit, Dean. "Take a seat." Dean gestured to the other side of the table and mentally slapped the shit out of himself. Cas sat down and smoothed down his tie (yeah, he was wearing a tie that he must have matched perfectly to his eyes) and smiled at Dean.  
 

     "Truthfully, I've lived around here for years and I've never been here. The only bar I frequent is my workplace. This place is quite nice, though." The moment Cas finished speaking, Dean burst out into laughter against his own volition. Cas stared at him with a confused look until he finally stopped to take a deep breath.  
 

     "Oh, wow," Dean wiped a tear from his eye, "That was...how in the world do you go from being a felon line cook to giving me college professor vibes and speaking like you belong in Hamlet? Don't get me wrong, it's great but...I mean you gotta-" Dean was stopped by Cas raising his hand in a 'let me explain' gesture.  
 

     "In my own defense, I was not always a felonious line cook." Cas was visibly uncomfortable so Dean stopped him.  
 

     "Don't worry. You don't have to explain yourself to me. You hungry?" At Cas' nod, Dean waved at the bar to get Jo to come over but was bitterly disappointed at who approached the table instead.  
 

     "Yo, Dean-o, Dr. Badass at your service! What can I get you and, more importantly, what can I get this tall, dark, and handsome glass of water you got here?" That's Ash...you know, come to think of it, Dean didn't know what Ash's last name is. He works for Jo's parents as their IT manager of sorts and he moonlights as a waiter on busy nights. This wasn't a busy night. He just loved to pop in his mullet-topped head in whenever Dean was in.  
 

     "One, don't objectify Cas. And B, your girl already called dibs on our order, Mullet Rat." Dean's voice was light on the nickname. Him and Ash were actually friendly, not friends nowadays per say, but friendly enough to joke with each other. Ash threw his hands up in a placating gesture and backed away from the table with a smile on his face.  
 

     "I get it, I get it. I'm not lookin' to sleep on the futon. I'll go get her. Catch you later and," Ash turned to Cas, "it was nice to meet you. I'm sure I'll see you again." Dean didn't even have to look at his 'date' to tell that he was blushing. Ash had a way of making anyone and everyone feel uncomfortable. Thankfully, Dean was pulled from his thoughts when Jo chirped from beside the table.  
 

     "Hey, Dean! Hey, Dean's handsome friend!" Jo cocked her hip out and looked at Dean with that smile that meant she was up to something.  
 

     "Geez, Jo. What is it with you guys and harassing my dates." Oh, fuck. Wrong word, Dean. "I mean my, uh, m-my friends. Yeah. My friends. Not my dates."  
 

     "Dean?" God, that voice is going to kill Dean one day.  
 

     "Yeah, Cas?"  
 

     "Stop talking."  
 

     "Yes." Dean chuckled to himself nervously as he refused to look at either Jo or Cas.  
 

     "Damn, Deanna. It has been a while. Cause Old Dean would never-"  
 

     "Joanna! Can we order now or would you like to pull out the baby pictures, hmm?" Dean looked at Jo with his eyebrows raised, both daring and asking her not to embarrass him even more than he embarrassed himself. Sensing the threat of Winchester retaliation, Jo backed down.  
 

     "No worries. What can I get you, guys?"  
 

     "Double bacon cheeseburger with extra onions, an order of fries, and a large Coke." A heavy silence fell over the trio, the only audible sound being the old football game coming from the television in the far corner. Dean sat gaping at Cas and Jo was gaping at the both of them.  
 

     "God, Dean, how have you not locked this shit down yet? He's like a more polite, more handsome, better dressed version of you. If you don't snatch him up, I will." Jo put the end of her pen in her mouth and smiled at the two men.  
 

     "Thank you for the compliment, Jo. However, I think it is impossible to be more handsome than Dean." Cas smiled across the table and Dean's heart almost fell out of his ass.  
 

     "Sa-same for me, Jo. Thanks." Dean shooed her away and looked back to the perfectly structured, 5 o'clock shadowed face across from him.  
 

     "So, Dean." Cas folded his hands on top of the table and, aw fuck, come on. Even the man's hands are fucking perfect. There's no way Dean is going to be able to go through with this.  
 

     "Cas, listen, I-" Dammit, Dean. You can't turn down that face. So what if he's attractive? Dean's attractive, too. He's not 'angelic supermodel' attractive but he's not ugly. He can't just dismiss Cas because of how he looks. No, that's a douche move. Okay, just suck it up, Dean. Maybe he'll back out before the night is over. "How are you?"  
 

     "Nervous." Cas snapped his mouth shut and took his hands off of the table. "I know it seems odd for me to be nervous considering that I made the advertisement and accepted you offer but I still am. I'm not used to meeting strangers in bars." Cas' face started to look like he might throw up.  
 

     "Woah, woah, calm down, buddy. Listen, nothing to be nervous about. You don't like strangers? Okay. Well, I'm Dean Winchester. I'm twenty-six and an Aquarius. I love my car and pie. I've got two brothers and Jo is my cousin. One time when I was little, I convinced my brother, Sam, that he could fly and he jumped off of the roof and broke his arm." Dean stopped and waited to see if that made Cas feel better or if he was still going to lose his stomach. Cas let out a breath he had probably been holding in since Dean started.  
 

     "Hello, Dean. I'm Castiel Novak. I'm twenty-eight and a convicted felon. I work at a gay bar. I've got two brothers and no high school degree. I haven't been to a family dinner in a little over ten years." Cas stopped to catch a breath when Jo approached their table, her hands holding a tray with their food and drinks.  
 

     "Here you boys go. Dean, Ash made your burger just the way you like it to apologize. He also wants to know if you want to play some video games sometime." Jo set all the plates and glasses on the table.  
 

    "Thanks, Jo. I'll-" Dean looked back at Cas, "I'll text him tomorrow." What? So what if Dean was hopeful that this night would go well. And no, Dean wasn't expecting sex. He was just hoping that Cas and he would get along well enough with each other to spend a few hours talking. When Dean looked back at Cas, the older man already had his burger halfway in his mouth and was letting out a moan that has no place outside of a bedroom.

  
     "Is that good or what?" Dean smiled and picked up his own burger, taking a huge bite. And yeah, Cas' moans were definitely deserved. Ash outdid himself by a longshot tonight.  
 

     "This is way better than what I make at Purgatory," Cas said around the food in his mouth.  
 

     "You work at Purgatory?" Purgatory was the only gay bar in the tiny town of Lawrence, Kansas and it was a goddamn hunting ground. Dean only ever had the courage to go their once, back when he had just graduated from high school and was newly eighteen and boy was that a mistake or what. He had never heard the word 'twink' more in his life.  
 

     "Yeah." Cas blushed and ducked his head. "It was the only place that would hire me when I got out.  
 

     "Geez, man, what did you do?" Stupid Dean and his stupid mouth. Come on, dude, that's not something you ask someone who has been to prison. For all you know, he could've murdered a man and now you're next.  
 

     "It's not a story I would like to share at this time." Cas' face fell and he took another bite of his burger.  
 

     "I'm sorry, Cas. I shouldn't have asked. That was dumb of me. I'm a dumb guy." Dean nervously chuckled.  
 

     "It's alright, Dean. Everyone asks. It's quite common." Cas still hadn't taken his eyes off of the table.  
 

     "So, would you rather talk about Thanksgiving?" Dean hoped he could grab Castiel's attention again. And it looks like that did the trick.  
 

     "Yes, please." Cas' head shot up and he looked at Dean expectantly.  
 

     "Well, it's at my parents' house, just on the outskirts of Lawrence. It will be them, us, my brother Sam, his wife Jess, my brother Adam, his boyfriend Michael, my Uncle Bobby, and my Aunt Ellen. They're Jo's parents but Jo won't be there so your cover won't be blown."  
 

     "That sounds alright. What kind of accompaniment are you looking for? Sex is off the table, by the way." Cas took a sip of his coke and leaned back in his seat, his stomach slightly distended from the food he scarfed down.  
 

     "Yeah, no, I totally get that. I just need you to pretend to be my boyfriend. My parents know I'm gay so it's not for the shock factor. I'm just really tired of showing up alone and having my parents and Sam try to 'help me' fix my love life. It's just annoying."  
 

     "I totally understand, Dean. So, what? Handholding, affection, a few kisses to really 'drive it home'?" Wow, he really just used air quotes while talking. That was more adorable than expected.  
 

     "Yeah, exactly." Dean smiled and picked his burger back up.  
 

     "I think this is going to be a good weekend, Dean. I look forward to it."

**Notes for the Chapter:**

> Tell me what you think!


	3. Thankful for Charlie

**Summary for the Chapter:**

> Best friend here to analyze your life and yell at you.

**Notes for the Chapter:**

> As always, please leave kudos and comments if you liked it (or if you didn't like it). I'm always open to constructive criticism but please keep it respectful.

     During their conversation at their initial meet-up, Dean and Castiel agreed to keep up with each other for the next two days and get the details of their fake relationship in order, since they will definitely have to provide details to Dean's family. Dean's mother, Mary, in particular is especially interested in her children's love lives. When Dean woke in the morning after his night with Cas, he rolled over and saw that his phone had a notification about a text from the other man.

  
 

 **Cas:** Good morning, Dean.

  
 

     Dean smiled to himself and got out of a bed, picking up a pair of sweatpants from his floor and throwing them on. He picked up his phone and typed a reply as he walked down his hallway on route to his kitchen.

  
**Dean:** Mornin' Cas. Sleep good?

  
     Dean set his phone on the counter and poured himself a bowl of cereal, smiling when he heard the text sound come from his phone.

  
_**Cas:**_ I slept very well, Dean. Did you?

 

 **Dean:** Hell yeah. Roadhouse food always makes me tired lol

 

 **Dean:** Also I feel like a total ass for talking the whole time last night.

                                                 I didn't really get to learn anything about you.

  
     Dean sat next to Honeybee and started eating his cereal, not bothering to turn the TV on. He was enjoying the silence. You could never get him to admit that he was worried if the TV was on then he wouldn't hear Cas text him back.    
 

     "Look at me, Honeybee. I'm a thirteen year-old girl."  
 

 _ **Cas:**_ Don't apologize, Dean. It's alright. You can ask me anything you want to know.  
 

     "Hmm. What do we want to know, Honeybee?" Dean looked at his kitten who just meowed in response. "Awesome ideas."  
 

 **Dean:** Hmm. Where in town do you live?  
 

 _ **Cas:**_ I live in a shared living space with a few employees at the bar. There's Kevin,  Gad, and Hannah.  
 

 **Dean:** No way! I know Kevin and Gad. They were friends with Sam growing up.

                                                 I don't know Hannah though. She works at Purgatory?  
 

     Dean didn't quite understand the premise of a woman working at Purgatory. It wasn't that they weren't allowed but it wasn't really a good scene, especially if you aren't a gay man.  
 

 _ **Cas:**_ Hannah work at the bar. HE is a bartender.  
 

 **Dean:** Ohhh okay. Gotcha lol.  
 

 _ **Cas:**_ I understand your confusion. Hannah is usually a woman's name.  
 

                                                  **Dean:** Yeah  
 

 **Dean:** So, what's your favorite color?  
 

 _ **Cas:**_ Green.  
 

 **Dean:** Favorite animal?  
 

 _ **Cas:**_ Cats. But only black ones.  
 

 **Dean:** Lol very picky  
 

 _ **Cas:**_ I also love bees.  
 

     Dean choked a little on his cereal. There are people who genuinely like bees? Interesting.  
 

 **Dean:** That's very interesting. I've never met someone who actually like bees.  
 

 _ **Cas:** _ Yes. I wanted to be a beekeeper as a child.  
 

 **Dean:** What happened?  
 

 _ **Cas:** _ Life.  
 

     Nice job, Dean. You made it depressing.  
 

 **Dean:** Ah shit man. I shouldn't have asked.  
 

 _ **Cas:**_ Don't fret Dean. It's not a big deal.  
 

                                                 **Dean:** Okay. Hey did you want to meet up a couple more times before Thanksgiving?

                                                 You know to get to know each other better because I know for a fact my family

                                                 will have a lot of questions.  
 

                                                  _ **Cas:**_ Of course. How about tomorrow for coffee @ Loki's

  
                                                   **Dean:** Sure! Does 2 work for you?

  
                                                   _ **Cas:** _ Of course. I'll see you then, Dean.

  
                                                   **Dean:** Sure will. Later Cas.

  
     Dean set his phone on the coffee table and took a bite of his cereal before humming his favorite song to himself. Maybe being around Cas for three whole days wouldn't be too bad. He seems easy to get along with and is more than easy on the eyes. Here's just to hoping that the rest of the Winchester clan is civil this year. While Dean was thinking, his phone started to ring, scaring Honeybee and causing her to dart out of the room. Dean looked at the Caller ID, picked up the phone, and put it to his ear.  
 

     "Handmaiden Dean here. How may I serve you today," Dean asked with the worst English accent in the world.  
 

     "The queen needs you to spill the details on why you were with a stunning man at the Roadhouse for four hours last night." That's Charlotte Celeste Bradbury, but she prefers Charlie or Queen of Moondoor. Dean and her met in high school and have been friends ever since. They even helped each other figure out that they were both 110% gay after an attempt at a hook-up in the 11th grade. Needless to say, the whole thing was a total disaster but they were able to laugh about it the next day.  
 

     "Cas is just a friend, Charlie. I'm allowed to have friends." Dean rolled his eyes and went in search of Honeybee, likely to find her under his bed.  
 

     "No you aren't, Dean. I'm literally your only friend. If you had another one, I would have known about it." Charlie let out a breath of false exasperation. "Now, tell me all about him." The conversation grew silent as Dean quarreled with himself. Sure, he could just tell her that Cas is his pretend boyfriend for Thanksgiving but then again, this is Charlie. Nothing is ever that simple with Charlie. She would undoubtedly find some way to accidentally mess it up.  
 

     "He's my boyfriend," Dean blurted out, "I didn't tell you about him because we're taking it slow...and he's shy..." Sure, Dean. That's certainly not going to raise any more questions. Idiot.  
 

     "Bitch, what?" Charlie's shrill voice gave Dean a sharp pain in his ear drum. "Your WHAT? Since when do you date? Since when do you talk to anyone besides me? Where did you meet? How long have you been together? What is his name?" Ah, yes. Nothing is simple with Charlie Bradbury around.  
 

     "His name is Cas. We, uh, we met at Pride a few months ago..." Hopefully that was good enough.  
 

     "No. I was with you at Pride. The only time your anxious ass left my side was to go get beers."  
 

     "Uh, yeah. He was in the bar with, uh...he was with his brother." Wow, Dean. You're a bad liar. If you can't pull it off with Charlie they're is no way you can pull it off in front of your whole family.  
 

     "Oh wait! I think I saw you talking to him! He's cute!"  
 

     "Sure is." Dean let out a nervous chuckle, thanking the gods that his friend filled in the rest of the lie for him.  
 

     "So, when do I get to meet him and do my bestfriend analysis?"  
 

     "Um, next weekend. We're going to my parents for Thanksgiving..."  
 

     "What?" Charlie's voice screeched in his ear. "I haven't even met him yet but your whole family gets to meet him for a whole freaking holiday weekend? Unfair. Unjust. I won't stand for it."  
 

     "It was kind of last minute, Char. His family...they, uh, they don't like him. They didn't invite him over for the holiday and I felt shitty leaving him to sit at home alone."  
 

     "Oh...well, okay. I'll accept that. But no one else is allowed to meet him before me," Charlie said petulantly.  
 

     "Alright, Charles. I'll make sure he doesn't go to any new restaurants or grocery stores between now and then. I'll talk to you later."  
 

     "Farewell, handmaiden." The incessant sound of a dial tone rang in Dean's ear after Charlie hung up, but was interrupted by a soft pinging noise. Pulling his face away from the screen, he saw that he had received three messages from his brother, Sam.  
 

 **Sam:** Mom said to bring pie.  
 

 **Sam:** You know, I could set you up with someone so you won't come to Thanksgiving alone.  
 

 **Sam:** Again.  
 

     Dean let out an exhausted breath and slumped into the pillowy cushions of his couch. Leave it to Sam freaking Winchester to be more involved in Dean's love life than he was. That Sasquatch of a boy meddled like it was a paying job and boy did he love when it messed up other people's lives. The last time Dean ever brought someone home, his name was Luke, Sam had run him off before dessert and then feigned ignorance like he had no clue that he had done something wrong.  
 

 **Dean:** No thanks, Sammy. I'm good.  
 

     Dean rolled his eyes and took a bite of his cereal.  
 

 **Sam:** Let me know if you change your mind. I still have Cole's number if you want it ;)  
 

 **Dean:** No way. That guys gives me the creeps. The whole military thing just reminds me of dad.  
 

 **Dean:** And don't ever send me a winky face again. I almost threw up in my frosted flakes  
 

 **Sam:** Sure thing big bro ;)  
 

 **Sam:** Oh btw Jess isn't coming this year.  
 

 **Dean:** Why not??  
 

 **Sam:** Long story. Tell you later. Gotta go, jerk.  
 

 **Dean:** See ya, bitch.

**Notes for the Chapter:**

> Let me know what you think so far!


	4. Thankful for Gadreel (and Ramen)

**Notes for the Chapter:**

> Well, I'm back! This update isn't very long but it's just something I wanted to get out quickly so no one would think I abandoned this work. Also, a reader suggested a chapter from Castiel's point-of-view so that's what this is. I hope you enjoy reading it and as always kudos and comments are much appreciated.

     No matter what anyone might try to tell you, Castiel Novak is not a loner. Just because he doesn't have any friends, only interacts with his roommates out of necessity, and has contemplated getting a cat just to have company does not make him a loner. It just means he's...lonely. But there's nothing wrong with that, right? People are lonely all the time. He's been alone for a long time. Ten years as of this Thanksgiving, to be exact. But for the first time in a long time, Castiel didn't want to be alone again. He didn't want to be sitting in front of his television, watching the Macy's Day Parade and eating his umpteenth pack of Ramen noodles. So, he did what any rational person would do. He posted an advertisement on Craigslist.

  
     It was a simple advertisement, no frills or bells or whistles. He didn't really even expect a response. It was sort of just a Band-Aid to make himself feel better. You see, recently Castiel had been feeling especially ostracized. Before, he didn't have that problem. Where he was, there wasn't any need to fit in. There wasn't any place to fit in so it wasn't a problem. But now? Out here in the real world? He was utterly lost and alone. It was pure luck that he happened to bump into his old friend, Gadreel, on the sidewalk once he got out of prison. He had already been homeless for six days and it didn't seem like it was going to get better. But, like an angel sent just for him, Gadreel offered him a job at the bar he owns and a room to stay in at his house, with his other roommates of course. He couldn't have been more grateful to his old friend for his selfless kindness and still thanks him at least once a week out of habit.

  
     His current arrangement isn't that bad. He works as a cook at Purgatory, Gadreel's bar, Gadreel takes rent out of his check, he buys Ramen, and then puts the rest of his money in an old coffee jar. He's saving for a place of his own, a place where he can have a cat and a garden. Because Gadreel's place is nice but New York City is too crowded and concrete for Castiel's taste. Sure, he's good at acting like a smooth-talking people's person when he needs to but on the inside he's constantly one millisecond from a panic attack. Maybe one day he'll get to where he wants to be but for now he's stuck. In the midst of his stewing in his loneliness, Castiel heard his phone buzz. He instantly picked it up and saw an unread email in his inbox.

  
     To: cnovak1977@gmail.com

  
     From: dwinchester67@gmail.com

  
     "Hello. I'm messaging you about the Thanksgiving thing. Just wondering if someone's  already filled the spot or if you're still free."

  
     "What?" Castiel blurted out into the empty apartment living room. He bent his knees and pulled his feet up onto the couch, folding in on himself as an unconscious attempt to avoid answering. To be fair, he didn't actually have to answer. Castiel could just close his email, put his phone down, and pretend it never happened...but, something inside him was telling him that he needed to respond. So, he did. And after a few messages back and forth, Dean (that's the guy's name, by the way) sent a picture of himself and just like that, Castiel's heart crumbled. There's no way that guy could be real. He had to have been a catfish. But, after twenty minutes of thorough reverse-image-searching, Castiel couldn't find any trace of false identity.

  
     Just when Castiel thought this situation couldn't get any better, he hit another roadblock. Dean asked for a picture of him. Of him. Now, that's a problem because Castiel Novak strongly considered himself to be the most self-conscious, insecure person in this realm of existence. No, really. Looking into a mirror makes him want to scream and he definitely doesn't do "selfies". But, once again, that small voice in his head was telling him that he needed to just send a picture or else he was going to regret it. So, he did and thankfully Dean is blind and thinks Castiel is aesthetically appealing. So now he has a "date". Awesome.


End file.
